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Volumn 60, Issue 39, 2004, Pages 8659-8668

Solid-phase synthesis of lamellarins Q and O

Author keywords

Cytotoxicity; Heteroaryl cross coupling; Marine natural products; Solid phase synthesis

Indexed keywords

ALKALOID; LAMELLARIN O; LAMELLARIN Q; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 4344599736     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.110     Document Type: Article
Times cited : (51)

References (53)
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    • WO 0164635 A1, 2001.
    • Boger, D. L. WO 0164635 A1, 2001.
    • Boger, D.L.1
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    • note
    • 2 and AcBr
  • 37
    • 4344691869 scopus 로고    scopus 로고
    • The crude cleavage material was analysed by HPLC and HPLC-MS
    • The crude cleavage material was analysed by HPLC and HPLC-MS
  • 39
    • 4344650539 scopus 로고    scopus 로고
    • Commercial 3-methoxyphenylboronic acid was used to find the best reaction conditions to be applied to the synthesis of lamellarins and derivatives
    • Commercial 3-methoxyphenylboronic acid was used to find the best reaction conditions to be applied to the synthesis of lamellarins and derivatives
  • 40
    • 4344564359 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the crude mixture by the singlet at 7.29 ppm due to the pyrrole proton 5
  • 41
    • 4344658108 scopus 로고    scopus 로고
    • 13C NMR of bisarylpyrroles 16b-16d were used to corroborate the introduction of the new aromatic ring
  • 42
    • 0034554740 scopus 로고    scopus 로고
    • The 4-isoproxoxyphenylboronic acid
    • The 4-isoproxoxyphenylboronic acid 15b was not commercial when we started this project. It was prepared from the p-iodophenol by protection with 2-iodopropane followed by boronic acid formation via halogen-metal interchange using nBuLi followed by reaction with trimethylboronate as described in Chaumeil H., Signorella S., Le Drian C. Tetrahedron. 56:2000;9655
    • (2000) Tetrahedron , vol.56 , pp. 9655
    • Chaumeil, H.1    Signorella, S.2    Le Drian, C.3
  • 43
    • 4344610978 scopus 로고    scopus 로고
    • 3 over the resin during 3 h allowed total recovery of the resin beads
    • 3 over the resin during 3 h allowed total recovery of the resin beads
  • 45
    • 4344710313 scopus 로고    scopus 로고
    • 3 as base and TBAF in THF or DMF, as described in solution in Ref. 6b, proved ineffective
    • 3 as base and TBAF in THF or DMF, as described in solution in Ref. 6b, proved ineffective
  • 46
    • 4344648626 scopus 로고    scopus 로고
    • note
    • 15 equiv. of NaH or 2 equiv. of LDA in dry THF at reflux for 24 h afforded, after cleavage, mixtures of 18a and 21a in which the alkylation product was obtained in 25% (NaH) and 30% (LDA) yield (HPLC-MS). Increasing the amount of LDA or the use of other bases did not improve the yield of 21a
  • 47
    • 4344702592 scopus 로고    scopus 로고
    • The compound was not isolated after trying different purification procedures on the crude cleavage material by semipreparative HPLC. The loss of material, probably by decomposition in the column
    • The compound was not isolated after trying different purification procedures on the crude cleavage material by semipreparative HPLC. The loss of material, probably by decomposition in the column
  • 48
    • 4344678823 scopus 로고    scopus 로고
    • 3 and 18-crown-6 as base in DMF in a microwave at 100 °C and 30-40 W during 2 min
    • 3 and 18-crown-6 as base in DMF in a microwave at 100 °C and 30-40 W during 2 min
  • 51
    • 4344594027 scopus 로고    scopus 로고
    • 3 and 18-crown-6 in DMF
    • 3 and 18-crown-6 in DMF
  • 53
    • 0001140874 scopus 로고
    • 1H NMR data were identical to those described in
    • 1H NMR data were identical to those described in Menger F.M. Chem. Soc. Rev. 1:1972;229
    • (1972) Chem. Soc. Rev. , vol.1 , pp. 229
    • Menger, F.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.